Total synthesis of (+)-virgatusin via AlCl3-catalyzed [3+ 2] cycloaddition

SD Sanders, A Ruiz-Olalla, JS Johnson

Index: Sanders, Shanina D.; Ruiz-Olalla, Andrea; Johnson, Jeffrey S. Chemical Communications, 2009 , # 34 p. 5135 - 5137

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Citation Number: 22

Abstract

The challenge of constructing the virgatusin core containing four contiguous stereocenters has been met by several groups. Yoda et al. completed the first synthesis of (−)-virgatusin. 6 The key step of Yoda's synthesis delivered the substituted tetrahydrofuran core via diastereoselective reduction of a cyclic hemiacetal intermediate (eqn (1)). Later syntheses by Yamauchi et al. 7 and Ghosh and Matcha 8 proceed through selective hydrogenolysis of a similar ...